Quaternary ammonium compounds



Patented June UNITHED TS'lATES P AT-ENT'i OFFICE-I ous'rnananr $221111! comoUNns Werner ze'rweck w mien, Frankforton-the-Main-Fec to General Aniline a Film Corporation, New

York; N. Y., a corporation of Delaware. p

No Drawing. Application August 6, 1940, Serial No. 351,644. In Germany August 19, 1939 4 Claims. The present invention'relates to new quaternary ammonium compounds. More particularly it relates to quaternary ammonium compounds prepared by acting with alhlating agents on such condensation products of phenolic compounds with aldehydes as are obtained by condensing one mole of a phenol, naphthol or hydrogenated phenolwith at least three moles of an'aldehyde in the presence of considerable amounts of ammonium salts which can also be replaced, in part,

4 by'amines.

The aforesaid initial materials employed for the manufacture of the present new quaternary ammonium compounds represent a special group within the well-known class of condensation products of phenols with-aldehydes. This special group of compounds the structure of which has, hitherto, not been found out and which is distinguished by remarkable new properties, has been described in the German Patent No. 686,988.

Owing to the fact that thecondensation of at least three moles of an aldehyde with one mole of a phenol is performed in the presence of considuct at a temperature of about 30, a considerable improvement or the fastness to washing of the after-treated dyeings is obtained.

erable amounts .of ammonium salts which, in

part, can also be replaced by amines, the con-1 densation products thus obtained exhibit the character of basic compounds. They are soluble in dilute acids and possess the property of precipitating from dilute aqueous solutions such organic dyestuffs as contain acidgroups; furthermore tanning matters and waste sulflte liquors.

In carrying out the present invention. the above described initial materials are treated with about 3 hours while stirring in an apparatus prosolution at about 20 to 25", with the simultaneous addition of sodium carbonate in order to keep the alkylatingagents according to known methods whereby valuabl new quaternary ammonium compounds are obtained which can be employed for various purposes. Inter 'alia, they v are distinguished by the valuable property of 1nv creasing considerably the fastness to washing of dyeings obtained on cellulose materials by means of substantive dyestuiis, when-such dyeings are after-treated with an aqueous solution. of one of the new quaternary ammonium-compounds.

* colored resin-like mass.

By aftertreating dyeings obtained on cellulose materials by meansof substantive dyestufl's for about 30 minutes with'an aqueous solution con-.

.ta'ined are dissolved in about parts of water.

lo'wish colored resin-likemass' by the addition of. concentrated alkali lye or by evaporating the uess to light is obtained by such an aftertreatment of dyeinss produced on cellulose materials Germ ny; more 10 parts of the condensation product thus obtained are dissolved in 60 parts of water. .Into

this solution 40 parts of dimethylsulfate are I slowly dropped in while stirring at a temperature of 20 to 25. In the meantime the reaction mixture is kept in a basic state by the addition of sodium carbonate. After the dimethyl sulfate has been dropped in, the mixture is further stirred for some 'hours at room temperature. Hereafter it is filtered. By evaporating the aqueoussolution to dryness or Ty adding concentrated alkali solutions the quaternary ammonium compounds formed are isolated as a yellowish taining 0.2 percent or the above alkylatins prod- Ezample 2 10 parts of phenol, 10 parts of ammonium sulfate, 5 parts of iso-heptylamine and parts of an'aqueous formaldehyde solution of 40 percent formaldehyde contents are heated to boiling for vided with a reflux condenser. a

- 10 parts of the condensation product thus o 40 parts of dimethyl' sulfate are dropped into this solutionv basic throughout the addition of the dimethyl sulfate. Hereafter the mixture is stirred I 'for some hours at room temperature.

The alkylating product obtained is isolated as a yelsolution until dry.

- For the purposeor aftertreating dyeings the .reaction solution canbe employed without'precedin: isolation of the quaternary ammonium'compound. A considerable improvement of the fast-v by means of substantive dyestuffs.

trample 3 denser;

parts of the condensation product thus obtained are dissolved in about 60 parts or water and then alkylated by adding 40 parts of dimethyl sulfate at about to with the aimultaneous addition of 20 parts of sodium carbonate. After stirring at room temperature for about 20 hours, an'alkylating product is obtained which can be isolated in the same manner as described in the foregoing examples. It can also be emf ployed without preceding isolation for the aftertreatment of dyeings whereby a considerable im,

provement of the fastness to washing is obtained.

' Example 4 10 parts of phenol, 10 parts of dimethyl-aniline, 10 parts of ammonium sulfate and 80 parts of an aqueous formaldehyde solution or 40 percent formaldehyde contents are heated to boiling for some hours whilestirring under a reflux condenser.

10 parts of the condensation product thus obtalned are dissolved in about parts of water and treated with 40 parts of dimethylsulafte as I methyl sulfate. I

described in the foregoing examples. Thereaction mixture obtained can also be employed as such for the improvement of the tastness properties of dyeings produced oncellulose materials by means of substantive dyestufls.

We claim:

1. Quaternary ammonium compounds prepared by peralkylating condensation products obtained by condensing one mole of a phenolic compound selected from the. group consisting of phenols and naphthols with at least three moles of an aliphatic aldehyde in the presence of a member selected from the group consisting of ammonium 3. Quaternary ammonium compounds as'defined in claim 1 wherein the peralkyiizlng is ef-' fected with dimethyl sulfate at a temperature of 20 to 25 C.

4. Quaternary ammonium compounds as definedin claim 1 wherein the peralkylizing is e1- fected with dimethyl sulfate at 20 to 25 C. in an aqueous solution of the condensation product to which sodium carbonate has been added to insure that the solution will remain alkaline.

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